Acetic Acid → HCID 53894318, compound

HRID 442450Notes

Reaction equation

HRID 442450 reaction equation
[OH:1][CH:2]1[CH:6]([O:7]C2CCCCO2)[CH2:5][CH:4]([CH:14]=[CH:15][CH:16]([OH:23])[CH:17]([CH3:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:3]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].C(O)(=O)C>O>[OH:1][CH:2]1[CH:6]([OH:7])[CH2:5][CH:4]([CH:14]=[CH:15][CH:16]([OH:23])[CH:17]([CH3:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:3]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 53827905HCID 53827905, compound

Product 1

HCID 53894318HCID 53894318, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 7-[2-hydroxy-5-(3-hydroxy-4-methyloct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (1.06 g.), glacial acetic acid (40 ml.) and water (20 ml.) was stirred at 40° C. for 4 hours. The mixture was then treated with water (50 ml.) and extracted with diethyl ether (2 × 50 ml.). The combined ethereal extracts were washed once with water, dried over magnesium sulphate, and concentrated in vacuo to low volume. Repeatedly, small portions of benzene were then added, concentrating in vacuo in order to remove last traces of acetic acid, and then the mixture was evaporated to dryness. The residue (0.5 g.) was subjected to preparative thin-layer chromatography on silica gel, using a mixture of ethyl acetate, cyclohexane and formic acid (40:40:1 by volume) as the eluent, to give 7-[2,3-dihydroxy-5-(3-hydroxy-4-methyloct-1-enyl)cyclopentyl]heptanoic acid (0.045 g.), νmax 1705 cm-1, 980 cm-1.

Workup

  1. extractionextracted with diethyl ether (2 × 50 ml.)
  2. washThe combined ethereal extracts were washed once with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo to low volume
  5. additionRepeatedly, small portions of benzene were then added
  6. concentrationconcentrating in vacuo in order
  7. customto remove last traces of acetic acid
  8. customthe mixture was evaporated to dryness
  9. additiona mixture of ethyl acetate, cyclohexane and formic acid (40:40:1 by volume) as the eluent

Sources & evidence

ORD record
ord-a6ef341c75dc41129ec8917b6190ff64
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

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