Dimethyl 4,4'-(3-oxopenta-1,4-diene-1,5-diyl)dibenzoate → HCID 14817494, compound

HRID 2082181Notes

Reaction equation

HRID 2082181 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:26])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[H][H]>C1(C)C=CC=CC=1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH:13]([OH:26])[CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1)([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 54403998Dimethyl 4,4'-(3-oxopenta-1,4-diene-1,5-diyl)dibenzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14817494HCID 14817494, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 175 g (0.50 moles) of 1,5-bis-(4'-carbomethoxyphenyl)1,4-pentadien-3-one, 1.75 g copperchromite, and 1750 mL of toluene were placed in a stainless steel autoclave. The autoclave was pressurized to 250 psi with hydrogen and then heated to 180° C. Upon reaching the desired temperature the pressure was adjusted to 1000 psig with hydrogen. The temperature and pressure were maintained at these levels for 5 h. The autoclave was then cooled and vented. The mixture was removed from the autoclave and transferred to a 2 L Erlenmeyer flask where the mixture was heated to >90° C. and then filtered through a steam jacketed Buchner funnel using a pad of Celite Filter-Aid to assist in catalyst removal. The solution was allowed to cool to room temperature and was filtered to give 142.1 g of 1,5-bis-(4'-carbomethoxyphenyl)-3-pentanol as a fluffy, white crystalline product. The volume of the mother liquor was reduced in vacuo to a level of 500-600 mL, heated to dissolve any solids, and crystallized to give an additional 13.9 g. Reducing the volume to 250 mL yielded an additional 5.2 g. All three batches of crystals were indistinguishable by chromatography and were combined to give a total of 161.2 g (0.453 moles, 91% yield) of 1,5-bis-(4'-carbomethoxyphenyl)-3-pentanol. 270 MHz 1H NMR (CDCl3) δ=1.81 (t,4H), 2.77 (m,4H), 3.61 (m,1H), 3.88 (s,6H), 7.21 (d,4H), 7.91 (d,4H). IR (KBr): 1720, 1290 cm1 ; (mull) 3460 cm1. FDMS (M+/e): 356. Elemental Analysis: Calc. for C21H24O5 : C,70.77; H,6.79. Found: C,71.09; H,6.68. m.p. 129°-130° C.

Workup

  1. temperatureThe temperature and pressure were maintained at these levels for 5 h
  2. temperatureThe autoclave was then cooled
  3. customThe mixture was removed from the autoclave
  4. temperaturewas heated to >90° C.
  5. filtrationfiltered through a steam
  6. customto assist in catalyst removal
  7. temperatureto cool to room temperature
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-496ef6b32a114f968c90eed5be08b179
Source dataset
uspto-grants-1993_02
Patent number
US05187304

Reaction notes

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