Water → HCID 59439459, compound

HRID 1640075Notes

Reaction equation

HRID 1640075 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[OH:15])(=O)[CH3:2].C/[C:17](=[CH:21]\[CH3:22])/[C:18]([OH:20])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:37]1(C)C=CC=CC=1.[OH2:44]>CS(O)(=O)=O>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:8]=1[O:15][C:21]([CH3:22])([CH3:37])[CH2:17][C:18]2=[O:20])(=[O:44])[CH3:2]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 14812Phosphorus oxide (P4O10)HCID 125468Tiglic acidHCID 59439471HCID 59439471, compound

Product 1

HCID 59439459HCID 59439459, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5.79 g (27.5 mmol) of 2-(2-hydroxy-6-methoxyphenyl)ethyl acetate, 3.03 g (30.3 mmol) of 2-methylcrotonic acid and 3.26 g (16.9 mmol) of diphosphorus pentaoxide in 29.0 mL of methanesulfonic acid was heated and stirred at 70° C. for 75 minutes. 50 mL of toluene and 50 mL of water were added therein at room temperature and the mixture was stirred for 5 minutes, and then transferred to a separatory funnel and settled. The aqueous layer was separated and discarded and after the organic layer was washed with 25 mL of 5% sodium hydrogen carbonate aqueous solution and 25 mL of water sequentially, the solvent was evaporated to obtain 7.85 g of the crude title compound. This was purified by silica gel chromatography (developing solution composition: 10% ethyl acetate-hexane (volume ratio), Rf: 0.4), and 2.96 g of the title compound was obtained.

Workup

  1. stirringat room temperature and the mixture was stirred for 5 minutes
  2. customtransferred to a separatory funnel
  3. customThe aqueous layer was separated
  4. washafter the organic layer was washed with 25 mL of 5% sodium hydrogen carbonate aqueous solution and 25 mL of water sequentially
  5. customthe solvent was evaporated
  6. customto obtain 7.85 g of the crude title compound
  7. customThis was purified by silica gel chromatography (developing solution composition: 10% ethyl acetate-hexane (volume ratio), Rf: 0.4)

Sources & evidence

ORD record
ord-7fddb4bc3c924c48adf9a469a56c34a9
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

Loading…